Here we would like to report a palladium-catalyzed coupling between monocyclopropanated pyrroles or furans and aryl halides or aryl boronic acids giving the corresponding six-membered N- and O-heterocycles. Key step of this transformation constitutes the selective cleavage of the non-activated, endocyclic C-C bond of the 2-heterobicyclo-[3.1.0]hexane framework triggered by a palladium chain walk. This protocol grants access to highly substituted piperidines and 2H-pyrans, that are challenging to synthesize by traditional methods. Furthermore, the synthetic application of the products was showcased by numerous transformations including the synthesis of a nipecotic acid derivative.

Regio- and stereoselective synthesis of functionalized dihydropyridines, pyridines, and 2H-pyrans: Heck coupling of monocyclopropanated heterocycles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.